Pyridine → 3-{4-[6-(4-Trifluoromethyl-phenyl)-3,4-dihydro-2H-quinolin-1-yl]-phenyl}-4H-[1,2,4]oxadiazol-5-one

HRID 1842032Notes

Reaction equation

HRID 1842032 reaction equation
[OH:1][NH:2][C:3](=[NH:30])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:19]3[C:14](=[CH:15][C:16]([C:20]4[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=4)=[CH:17][CH:18]=3)[CH2:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1.N1C=CC=CC=1.[C:37]1([O:43]C(Cl)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>ClCCl.C(#N)C>[F:29][C:26]([F:27])([F:28])[C:23]1[CH:24]=[CH:25][C:20]([C:16]2[CH:15]=[C:14]3[C:19](=[CH:18][CH:17]=2)[N:10]([C:7]2[CH:8]=[CH:9][C:4]([C:3]4[NH:30][C:37](=[O:43])[O:1][N:2]=4)=[CH:5][CH:6]=2)[CH2:11][CH2:12][CH2:13]3)=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178513334HCID 178513334, compound

Product 1

HCID 1359265213-{4-[6-(4-Trifluoromethyl-phenyl)-3,4-dihydro-2H-quinolin-1-yl]-phenyl}-4H-[1,2,4]oxadiazol-5-one

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

355 mg crude N-Hydroxy-4-[6-(4-trifluoromethyl-phenyl)-3,4-dihydro-2H-quinolin-1-yl]-benzamidine were dissolved in 4 ml dichloromethane. 73 μl pyridine and 113 μl phenylchloroformate were added and the mixture stirred at room temperature for ten minutes. The mixture was diluted by the addition of 4 ml acetonitrile and 558 μl 1,8-diazabicyclo[5.4.0]undec-7-ene were added. The mixture was stirred at room temperature for 15 minutes. The mixture was evaporated in vacuo and the resulting crude material was purified by reversed phase HPLC to obtain 209 mg 3-{4-[6-(4-Trifluoromethyl-phenyl)-3,4-dihydro-2H-quinolin-1-yl]-phenyl}-4H-[1,2,4]oxadiazol-5-one.

Workup

  1. additionwere added
  2. stirringThe mixture was stirred at room temperature for 15 minutes
  3. customThe mixture was evaporated in vacuo
  4. customthe resulting crude material was purified by reversed phase HPLC

Sources & evidence

ORD record
ord-a522315c9ae84114a6b3d1e13d30dd4d
Source dataset
uspto-grants-2015_02
Patent number
US08946212B2

Reaction notes

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